We report the use of hydroquinone as a Chemoselective Redox Responsive Linker (CRRL), which serves as a site for bioconjugation, and subsequently, as a cleavable linker at physiological condition controlled electrochemically. Upon oxidation, the quinone conjugates an oxyamine group, or CRRL ligand. By applying potential in reducing conditions, the ligation can be broken to reveal the hydroquinone. Potential biological applications are demonstrated by synthesizing a peptide, RGD, which contains a HQ-tethered amino acid that is capable of intramolecular and intermolecular CRRL reactions. We have extended this chemistry to probe the effects of presenting two ligands from the surface: cell adhesive peptide, GRGDSS and a variable biomolecule on cell adhesion, morphology, size, and migration rate. With a dynamic, dual ligand system that can release ligands in the presence of cells, we aim to investigate the synergistic effects of tethering peptide PHSRN and sugars galactose and mannose with RGD on cell behavior.

Dual ligand-presenting surfaces that can dynamically modulate cell behavior in situ

240th National Meeting (2010)

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